Enantioselective synthesis of dihydro-1H-benzindoles
Gustavo P Silveira1, Joseph P Marino
1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA. gustavo.silveira@iq.ufrgs.br
Abstract:
The first examples of dihydro-1H-benzindoles by enantioselective γ-lactamization reaction of naphthyl sulfilimines with trichloroacetyl chloride in the presence of ZnCu as catalyst (≥98:2 er and 65-80% yields) are described. Products are obtained by [3,3]-sigmatropic rearrangement of the azasulfonium enolate or followed by a second allylic rearrangement that transfers chirality. The absolute stereochemistry was confirmed by X-ray crystallography, which provides support for the mechanisms proposed.
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